Amyl nitrite



Amyl nitrite
IUPAC name 3-methyl-1-nitrosooxybutane
Other names Isoamyl nitrite
Nitramyl
3-methyl-1-nitrosooxybutane
Pentyl alcohol nitrite(ambiguous)
Nitrous acid, pentyl ester(ambiguous)
Identifiers
CAS number 110-46-3
RTECS number NT0187500
SMILES CC(C)CCON=O
Properties
Molecular formula C5H11NO2
Molar mass 117.15 g/mol
Appearance Colourless liquid
Density 0.872 g/cm³, liquid (25 °C)
Melting point

?? °C

Boiling point

99 °C

Solubility in water Low
Hazards
Main hazards vasodialator
Flash point 21 °C
Related Compounds
Related compounds Isobutyl nitrite
Ethyl nitrite


Methyl nitrite
Isopropyl nitrite
Cyclohexyl nitrite

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Amyl nitrite is the vasodilator which is the basis of its use as a prescription medicine. As an inhalant, it also has a psychoactive effect which has led to illegal drug use.

Nomenclature

The term "amyl nitrite" encompasses several conformation.

Amyl nitrite is often confused with amyl nitrate, a substance with a different chemical composition and different properties.

Synthesis and reactions

Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:[1]

C5H11OH + HONO →→ C5H11ONO + H2O

The reaction is called esterification. Synthesis of alkyl nitrites is generally straightforward and can be accomplished in home laboratories. A common procedure includes the dropwise addition of concentrated sulfuric acid to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. The intermediately formed stoichiometric mixture of nitrous and nitric oxide then converts the alcohol to the alkyl nitrite, which, due to its low density, will form an upper layer that can be easily decanted from the reaction mixture.

Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol:

C5H11ONO + NaOH → C5H11OH + NaNO2

Amyl nitrite, like other alkyl nitrites, reacts with oximes.[2]

Physiological effects

Amyl nitrite, in common with other Overdose symptoms include nausea, emesis (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting). The effects set in very quickly, typically within a few seconds and disappearing soon after (within a minute).

It induces the formation of methemoglobin, which sequesters cyanide as non-toxic cyanomethemoglobin.[4]

Applications

Amyl nitrite is employed medically to treat heart diseases such as angina and to treat Poppers.

References

  1. ^ Noyes, W. A. “n-Butyl Nitrite” Organic Syntheses, Collected Volume 2, p.108 (1943). [1] (PDF)
  2. ^ Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. “(2S)-(-)-3-exo-(Morpholino)isoborneol ((-)-MIB)” Organic Syntheses, Volume 82, pp. 87 (2005). [2] (PDF)
  3. ^ Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson. Isobutyl Nitrite and Related Compounds. 1st ed. San Francisco: Pharmex, Ltd, 1979. [3]PDF
  4. ^ Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?". Toxicology 168 (1): 37-38.
  5. ^ Cheng, L.; Goodwin, C. A.; Schully, M. F.; Kakkar, V. V.; Claeson, G. (1965). "The Effects of Nitroglycerin and Amyl Nitrite on Arteriolar and Venous Tone in the Human Forearm". Circulation 3 (2): 755.
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Amyl_nitrite". A list of authors is available in Wikipedia.